The present invention relates to derivatives of 1-hydroxy-2-naphthalenecarboxylic acid (1-hydroxy-2-naphthoic acid) and BON acid (3-hydroxy-2-naphthalenecarboxcylic acid; 3-hydroxy-2-naphthoic acid; or .beta.-oxynaphthoic acid) having a poly(oxyalkylene) substituent, and in particular to poly(oxyalkylene) substituted amide derivatives of such acids. The scope of the invention also includes azo colorants which incorporate the hydroxynaphthalenecarboxylic acid derivatives as a coupling component.
The use of hydroxynaphthalenecarboxylic acid as a coupling component in azo colorants is well known. For example, Lithol Rubine (Pigment Red 57), Permanent Red 2B (Pigment Red 48), Yellow BON Maroon (Pigment Red 55), and Lithol Red 2G (Pigment Red 52) are all synthesized by coupling the diazonium salt of a primary aromatic amine to BON acid.
Arylamides of BON acid have also been employed as azo coupling components, such as Naphthol AS. Azoic or naphthol pigment dyes made from these arylamides have been found to have greater substantivity for cotton than those made with the corresponding BON acid component. Examples of arylamides of BON acid may be found in Marriott, et al., U.S. Pat. No. 2,328,734 and Glendill et al., U.S. Pat. No. 3,034,892. Amides of BON acid and either benzylamine or phenylethylamine are disclosed in Hirasawa et al. U.S. Pat. No. 5,286,287. The coupling components are useful in manufacturing monoazo pigments for printing inks.
Disazo colorants may be made from amide derivatives of BON acid. Two moles of BON acid are first convened to the acid chloride, followed by condensation with an aromatic diamine. Dahlen, U.S. Pat. No. 1,987,669 discloses a BON acid and aromatic diamine condensation product which is useful as a dye intermediate for disazo colorants. The aromatic diamines may be linked by a diethylether group.
Further examples of amide derivatives of hydroxynapthalenecarboxylic acid which have an ether constituent may be found in the following patents: Bossard, et al., U.S. Pat. No. 3,207,748--intermediates for hydrophobic azo dyestuffs; Umberger, et al., U.S. Pat. No. 3,299,013--vinyl containing dye intermediates for use in color photography; and Yoshida et al., U.S. Pat. No. 3,644,518--process for producing 1-hydroxy-2-naphthamide derivatives. The aforementioned dye intermediates illustrate up to two oxyalkylene groups in the amide substituent.
Colorants and colorant intermediates having poly(oxyalkylene) substituents are disclosed in the following patent publications: Toyo, Ink., Japanese Kokai Patent No. 63[1989]-264674--pigment having improved dispersability; Schwartz, et al., U.S. Pat. No. 4,468,255 and Schwartz, et al., U.S. Pat. No. 5,062,894--poly(oxyalkylene) modified arylide and diarylide pigments; Moore, et al., U.S. Pat. No. 5,176,745--aqueous ink compositions; and Moody, et al., U.S. Pat. No. 5,290,921--intermediates and colorants having branched poly(oxyalkylene) substituents. These colorants have found applications in areas of inks, fugitive tints for textiles, thermoplastic resins and thermosetting resins.
Although a large number of poly(oxyalkylene) substituted colorants appear in the prior art, a poly(oxyalkylene) substituted derivative of hydroxynaphthalenecarboxylic acid or azo colorant made therefrom has not been disclosed. In the typical synthesis of amide derivatives of hydroxynaphthalenecarboxylic acid, the dye intermediate is recovered by crystallization and filtration. However, the enhanced solubility and liquidity of typical poly(oxyalkylene) substituted intermediates and colorants have deterred adoption of such prior art techniques. Thus, despite the extensive use of hydroxynaphthalenecarboxylic acid and amide derivatives of hydroxynaphthalenecarboxylic acid in the manufacture of colorants, a poly(oxyalkylene) substituted derivative of hydroxynaphthalenecarboxylic acid or an azo colorant made therefrom, has not been heretofore available. All of the aforementioned patents are incorporated herein by reference.